Triethylamine → 4-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile

HRID 1161542ノート

反応式

HRID 1161542 の反応式
[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C(N(CC)CC)C.C[O:17][C:18](=O)[N:19]=[C:20](SC)[C:21]([C:31]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:32]=1[F:50])=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1.[B-]C#N.[Na+]>C1COCC1.C(OCC)(=O)C.C(O)(=O)C.CO>[Si:43]([O:42][CH2:41][CH2:40][O:39][C:33]1[C:32]([F:50])=[C:31]([CH:21]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[C:20]2[NH:19][C:18](=[O:17])[N:1]([C:3]3[N:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[N:2]=2)[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=1)([C:46]([CH3:48])([CH3:49])[CH3:47])([CH3:45])[CH3:44]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 3465582-HydrazinylpyrimidineHCID 20587905Sodium cyanoborohydride [MI]HCID 72312754(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

生成物 1

HCID 1359820434-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile収率 105.5%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

After adding 600 mg of 2-hydrazinopyrimidine and 1.5 ml of triethylamine to a solution of 3.2 g of (2-{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester in 30 ml of THF, the mixture was stirred overnight at 60° C. under a nitrogen atmosphere. Next, 30 ml of methanol and 4.5 ml of acetic acid were added to the reaction mixture. After then adding 3 g of sodium cyanotrihydroborate to the solution, the mixture was stirred at room temperature for 5 hours. Ethyl acetate was added to the reaction mixture. After washing the organic layer with water and saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure to give the title compound (3.4 g, crude product) as a light yellow solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. washAfter washing the organic layer with water and saturated brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-6f1d0c81ee324a37ab7528d714169484
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

読み込み中…